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Luxury Awaits at Mainsail! Dock, Spa, Pool and Steps to Siesta Key Beach!

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A two-story house with a swimming pool, outdoor furniture, and a covered patio area.
A poolside area with lounge chairs and a view of a waterfront with palm trees and buildings.
A spacious living area with a wooden staircase, a large TV, and a cozy seating area with patterned cushions.
A room with three windows overlooking a body of water, a boat, and palm trees.
A spacious kitchen with white cabinetry, a large island with a sink, and a built-in oven.

Reviews

9.8 out of 10
Exceptional

Entire home

4 bedrooms4 bathroomsSleeps 102919 sq ft

Popular amenities

  • Pool
  • Hot tub
  • Kitchen
  • Washer
  • Dryer
  • Free WiFi

Explore the area

View in a map
Siesta Key, FL
  • Place, Siesta Key Beach
    ‪6 min walk‬
  • Place, Safe Harbor Siesta Key
    ‪15 min walk‬
  • Place, Crescent Beach
    ‪16 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪27 min drive‬

Room options

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  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
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About the neighborhood

Siesta Key

When you stay at this vacation home in Siesta Key, you'll be on the waterfront, a 2-minute drive from Siesta Key Beach and 8 minutes from Crescent Beach. .This vacation home is 10.2 mi (16.4 km) from St. Armands Circle and 11.8 mi (19 km) from Lido Beach.
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What's nearby

  • Siesta Key Beach - 6 min walk - 0.4 miles
  • Safe Harbor Siesta Key - 15 min walk - 0.9 miles
  • Crescent Beach - 16 min walk - 0.9 miles
  • St. Boniface Episcopal Church Labyrinth - 4 min drive - 1.5 miles
  • Siesta Key Beach Playground - 4 min drive - 1.5 miles

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 35 min drive

Restaurants

  • ‪McDonald's - ‬3 min drive
  • ‪Captain Curt's Crab & Oyster Bar - ‬14 min walk
  • ‪Hooters - ‬4 min drive
  • ‪Daiquiri Deck South Siesta Key - ‬13 min walk
  • ‪Spear Fish Siesta Grill - ‬16 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Luxury Awaits at Mainsail! Dock, Spa, Pool and Steps to Siesta Key Beach!

Mainsail by Siesta Key Luxury Rental Properties

Mainsail by Siesta Key Luxury Rental Properties is a breathtaking 4 bedroom, 3 and a half bath waterfront luxury home with a bonus room, private dock, and spectacular Intracoastal Waterway views. Nestled at the end of a quiet street and just a 10-minute walk to Crescent Beach, this upscale retreat offers a refined yet relaxed coastal lifestyle perfect for large families and groups. With a private pool, in-ground spa, multiple outdoor lounges, and seamless indoor and outdoor living. Mainsail sets the stage for an unforgettable Siesta Key luxury rental experience near South Siesta Key Village.

Highlights
• 10-minute walk to Crescent Beach
• 4 Bedrooms / 3.5 Bathrooms
• 3 King beds, 2 Queens
• Private dock (18 ft)
• Private heated pool and in-ground spa
• 2 kayaks included
• Outdoor bar and outdoor kitchen
• Covered outdoor dining and lounge areas
• Wet bar and wine fridge
• 5 parking spaces

Designed for waterfront relaxation, Mainsail features a private heated pool, a spa, and wide poolside terraces capturing panoramic waterway views. Enjoy evening cocktails at the outdoor bar, prepare meals in the covered outdoor kitchen, or gather for sunset dining on the balcony overlooking the Intracoastal. With two kayaks included, guests can explore the calm waterway right from the private dock. Every outdoor space is crafted for comfort, inviting you to unwind in a true tropical outdoor oasis.

Inside, Mainsail offers a bright and expansive open concept layout with designer inspired coastal interiors. Floor to ceiling windows frame sparkling water views throughout the living and dining areas, while the gourmet kitchen features high end appliances, generous counter space, and island seating ideal for group gatherings. The dining table seats nine comfortably for shared meals, and an additional wet bar with a wine fridge enhances the luxury entertaining experience. Multiple lounge areas, and beautiful hardwood floors throughout, create a warm, elevated atmosphere.

Retreat to the luxurious second-floor primary suite, complete with a California king bed, ensuite bathroom, double vanity, walk-in shower, and walk-in closet, plus a convenient mini refrigerator. On the main floor, two guest suites offer king beds and private ensuite bathrooms, one with a shower/tub combination and one with a walk-in shower. A fourth bedroom includes two queen beds, making it ideal for families or additional guests. The bonus room features a twin daybed, offering a space for relaxing or flexible use. All rooms are designed with calming coastal finishes to ensure a restful stay.

Room Details
-Primary Bedroom (2nd floor): King bed, ensuite bathroom with double vanity + walk-in shower
-Second Bedroom (1st floor): King bed, ensuite bathroom with shower/tub combo
-Third Bedroom (1st floor): King bed, ensuite bathroom with walk-in shower
-Fourth Bedroom (1st floor): Two Queen beds

This home includes a private dock, kayaks, outdoor bar, outdoor kitchen, multiple waterfront terraces, balcony seating, covered lounges, wet bar, and extensive space for up to five vehicles. Located near South Siesta Key Village, guests are close to shops, nightlife, restaurants, and beautiful Siesta Key Beach.

Mainsail by Siesta Key Luxury Rental Properties is a rare blend of waterfront elegance, luxury amenities, and prime island location. From its private dock and expansive outdoor spaces to refined interiors and incredible waterway views, this home offers the perfect setting for a memorable Siesta Key escape.

Book your stay at Mainsail today and experience the best of waterfront luxury on Siesta Key!

-
This home is managed by Siesta Key Luxury Rental Properties.

This property does not allow pets of any kind.

This property has active video surveillance on the exterior public approach areas and the pool equipment.

5 cars maximum are able to park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age. Please see our Siesta Key Luxury Rental Properties Rental Policies for full details.

Please Remember: "You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a Smart TV. There's a private balcony. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access is available to keep you connected.
Enjoy the recreation opportunities such as a hot tub or make use of other amenities including barbecue grills.
Guests will find features like internet access and onsite parking.

Property amenities

Pool/Spa

  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 3.5 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard

Laundry

  • Laundry facilities
  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near the marina
  • Near the sea
  • On the waterfront

Things to do

  • Heated pool
  • Kayak
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Swimming nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Unit size: 2,919 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

Mainsail Four Bedroom House Sleeps 10
ON THE Intercoastal 4 bedroom Luxury Home w/ Private Pool Spa!
29

Luxury Awaits at Mainsail! Dock, Spa, Pool and Steps to Siesta Key Beach! Reviews

Reviews

9.8

Exceptional

Rating 10 - Excellent. 32 out of 37 reviews
Rating 8 - Good. 5 out of 37 reviews
Rating 6 - Okay. 0 out of 37 reviews
Rating 4 - Poor. 0 out of 37 reviews
Rating 2 - Terrible. 0 out of 37 reviews

9.8/10

Cleanliness

Reviews

Verified

10/10 Excellent

Verified traveler

Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic house and location
Stayed 5 nights in Feb 2026
Verified

10/10 Excellent

Kip E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful view

Excellent vacation!
Stayed 6 nights in Dec 2024
Verified

10/10 Excellent

Craig S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

A great stay

A great property - beautiful views, pristine condition, perfect for our family of 4 with room to spare.
Stayed 4 nights in Jun 2022
Verified

10/10 Excellent

Maribel H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

The house was amazing! Everything was super clean and is very close to Siesta Key beach. We loved it

The renting experience was easy and great.
Stayed 5 nights in Sep 2022
Verified

10/10 Excellent

Andrew H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Holiday Stay

Beautiful Open Space with Dolphins Swimming by the Deck. Amazing Location Great Support
Stayed 7 nights in Dec 2023
Verified

10/10 Excellent

Michelle M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Lovely home

Great location to relax with a group
Stayed 3 nights in Jul 2022
Verified

10/10 Excellent

Ann S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Landing place for memorial service

We had 7-9 guests (3 under seven years of age) and found the property wonderful and well supplied. We especially enjoyed the pool and kayaks. Plenty of room for family meals.
Stayed 5 nights in Oct 2023
Verified

10/10 Excellent

ANdrea P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great home

Very nice property for family get together. Ages 10-84 did well!!!
Stayed 6 nights in Jul 2024
Verified

10/10 Excellent

Jennifer w.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Intercostal gem!

Our family thoroughly enjoyed our stay in this beautiful home on the inter coastal waters. We loved being able to rent a boat, fish and kayak off of the dock. The walk to the beach was a little further than expected but doable. Amazing home for our group of 7 adults.
Stayed 5 nights in May 2025
Verified

10/10 Excellent

lance D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Relaxing spot

The house is wonderul. Right on the bay and the amenities are all top of the line. I would rent it again.
Stayed 5 nights in Sep 2021
Verified

10/10 Excellent

kawveh n.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Siesta Key 2023

Excellent week at the house! Very relaxing! Gots all the amenities! Great views!
Stayed 7 nights in Mar 2023
Verified

8/10 Good

Jeff O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Spring break 2024

Great expererience
Stayed 6 nights in Apr 2024
Verified

10/10 Excellent

Sallie V.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Outstanding Family Experience

“Over the top”!!!
Stayed 8 nights in Nov 2024
Verified

10/10 Excellent

Kevin W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome , Gorgeous Clean House !!!!

We stayed 6 nights and everyone in my family of 10 were so happy and excited to stay in such a beautiful, gorgeous house right on the waterway and blocks from beach. Thank you management for quick responses.
Stayed 6 nights in Sep 2024
Verified

10/10 Excellent

Justin D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Awesome property

Wife, kids (8 and 6) and I had a blast staying at this property. The pool, hot tub, and dock access for my kids to fish were our favorites. Awesome sound system to listen to music while floating in the pool and great outdoor tv (huge) to watch March Madness. Massive kitchen with all the utensils needed. Highly recommend!
Stayed 7 nights in Mar 2024
Verified

10/10 Excellent

Wayne H.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Siesta key stay

Very nice property. Great views of the waterway and relaxing outdoor area. Only gripe was there was no dishwasher detergent or any soap to clean the dishes. We’ve stayed at other VRBOs that had much more miscellaneous Kitchen and bathroom supplies.
Stayed 7 nights in Feb 2023
Verified

10/10 Excellent

Elzan O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect location

My family stayed at the house for 12 days. The view from the pool was beautiful and to watch the boats pass by. The house had bikes to use and a beach cart. Public beach was walkable. House was in perfect shape. We all enjoyed the kayaks and went fishing, fishing poles were also at the house.
Stayed 9 nights in Dec 2022
Verified

10/10 Excellent

Ed T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Vacation

Terrific house that is very well maintained. The kayaks, pool, and fishing dock were fantastic giving everyone lots to do. Tons of living space outdoors and in. Sitting on the balcony for our meals watching the boats and wildlife was so relaxing. Unfortunately, we had multiple issues with the bikes. I understand that the management company switched to a new bike vendor and were working out some issues. Overall a great experience and trip.
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

Meghan M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Vacation Home Siesta Key

Absolutely beautiful vacation home! We had the most relaxing week during our stay. We’d have coffee every morning on the deck watching the boats and dolphins swim by. The house itself is stunning! Beautifully decorated, comfortable beds, large sofa that all 7 of us could relax on later in the evenings. The pool was amazing. Our kids swam from early morning until late in the evening. The staff were very prompt in their responses and very pleasant to deal with. I would definitely stay in this vacation home again and highly recommend for any family to stay here!
Stayed 6 nights in May 2024
Verified

10/10 Excellent

Karen T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect stay!

The property is as described (+); the home is beautiful and very clean. The location is perfect. Its a short walk to the beach, dining, stores. There's a shuttle stop at the end of the long driveway. Dolphins graced our presence every day. Beautiful views of sunrise and sunset. Easy check-in and out. The hot tub was nice (I was surprised how warm it was given how cold it has been)... The temp in the house was comfortable (again, surprised that the home is set and maintained at a cool temp given how big the place is). All around perfect stay!
Stayed 5 nights in Feb 2024
Verified

10/10 Excellent

Rod M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Mainsail was great

Beautiful and quiet. Hated to leave, it was so peaceful but great fun at same time. Pool, jacuzzi, arcade game for kids, games, kayaks, bikes- we used it all. Saw dolphins in Robert’s Bay on two occasions as well. Prop Mgmt was very responsive. Could use a Dyson for quick clean ups. Outside space is top notch.
Stayed 7 nights in Mar 2023
Verified

10/10 Excellent

Kate E.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Amazing Home

This house is amazing. The location can’t be beat. We had a great time. The pool/spa heater was giving us issues but the Property manager was always quick to respond and send someone to fix. Our only complaint is the bedrooms on the ground level have very hard beds. My kids ended up sleeping on the large comfy living room couch.
Stayed 5 nights in Nov 2020
Verified

10/10 Excellent

Cherie G.

Liked: Cleanliness, check-in, communication, location, listing accuracy
12/10 recommend this place! Check in was easy and my two minor concerns (one of which turned out to be a me problem not a them problem) were addressed very quickly. The pool was used constantly! There was some sort of leak causing it to get green quicker than usual but it was addressed twice during our stay and the kids couldn’t have cared less regardless. The started sets came in handy since we got in late.Some things to note for your own stay: - The rear doors have very loud alarms. This is a requirement but we weren’t aware and immediately set them off when we arrived and then sat covering our ears for a solid 5 minutes until we were informed it’s a simple button push right on the alarms to silence them every time you use them. No big deal from that point on!-There was a beach wagon, chairs and towels but no other beach items for families. We bought some boogie boards, buckets and shovels and left them there for other families to enjoy! Pulling the loaded wagon on the beach was a treat, just plan to have someone push while another person pulls!-The beach is close and you could probably bike or walk depending on your guests and how much stuff you have. We drove and public parking was kind of a nightmare at certain times. The largest parking area is by Siesta Key Beach but if you try to go between 10-3 (season depending I’m sure) you’ll drive around in circles for 15 mins before you get lucky and someone pulls out.Overall we would 100% stay here again and again!
Stayed 5 nights in Mar 2026
Verified

10/10 Excellent

Katie M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Absolutely amazing

This property is amazing! It completely exceeded our expectations for our family getaway. We had plenty of room (5 adults and 4 kids). The details in the kitchen and around the house, the fabulous views throughout the house, and the luxurious master bedroom and bath blew us away. We thoroughly enjoyed spending time at the pool and in the various outdoor spaces watching the boats go by. And the huge tv on the covered porch was the perfect spot to watch the NFL playoff games. Also, the property manager was extremely friendly and helpful and the check in/ check out process was super easy. Honestly couldn’t have asked for more. 10/10 recommend!
Stayed 5 nights in Jan 2021
Verified

8/10 Good

Todd A.

Liked: Check-in, location, listing accuracy

This is a great house

We where a family of 9 with little kids, teenagers and adults. The house was very comfortable with plenty of room for everyone. The kitchen is huge with a large Frig/Frezer along with small refrigerators throughout the house. There could have been better / more cooking items but we made due. Also, there are no condiments or anything left in the house so make sure you bring everything you need. Beds were good but the towels are terrible, we ended up going to target to get towels to use for the week, maybe we are brats, lol. Overall great house would definitely rent it again. Location is great, waterway in the back with boat dock was perfect and less than a 10 min drive to Siesta Key Beach.
Stayed 7 nights in Jul 2022